ArticleChemistry (Weinheim an der Bergstrasse, Germany)2018
Synthesis and Self-Assembly of Bay-Substituted Perylene Diimide Gemini-Type Surfactants as Off-On Fluorescent Probes for Lipid Bilayers.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 27 citations in OpenAlex.
- Modulating the photophysical properties of perylene-based light-harvesting materialsRSC advances · 2026Article
- Enhancing Humidity Sensing with Functionalized Perylene-Coated Dispense Printed Electrodes: A Comparative Study.ACS applied electronic materials · 2025Article
- Recent Advances in Applications of Fluorescent Perylenediimide and Perylenemonoimide Dyes in Bioimaging, Photothermal and Photodynamic Therapy.International journal of molecular sciences · 2023Review
- Perylene-Based Chromophore as a Versatile Dye for Light Amplification.Materials (Basel, Switzerland) · 2022Article
- Tetrahydroxy-Perylene Bisimide Embedded in a Zinc Oxide Thin Film as an Electron-Transporting Layer for High-Performance Non-Fullerene Organic Solar Cells.Angewandte Chemie (International ed. in English) · 2019Article
- Mutually Exclusive Cellular Uptake of Combinatorial Supramolecular Copolymers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Synthesis and Self-Assembly of Bay-Substituted Perylene Diimide Gemini-Type Surfactants as Off-On Fluorescent Probes for Lipid Bilayers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Interest in bay-substituted perylene-3,4:9,10-tetracarboxylic diimides (PDIs) for solution-based applications is growing due to their improved solubility and altered optical and electronic properties compared to unsubstituted PDIs. Synthetic routes to 1,12-bay-substituted PDIs have been very demanding due to issues with steric hindrance and poor regioselectivity. Here we report a simple one-step regioselective and high yielding synthesis of a 1,12-dihydroxylated PDI derivative that can subsequently be alkylated in a straightforward fashion to produce nonplanar 1,12-dialkoxy PDIs. These PDIs show a large Stokes shift, which is specifically useful for bioimaging applications. A particular cationic PDI gemini-type surfactant has been developed that forms nonfluorescent self-assembled particles in water ("off state"), which exerts a high fluorescence upon incorporation into lipophilic bilayers ("on state"). Therefore, this probe is appealing as a highly sensitive fluorescent labelling marker with a low background signal for imaging artificial and cellular membranes.
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Registered trials
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